A Book to Inspire Your Chicago Bucket List

After living in the city for seven years, it might be surprising that my Chicago bucket list is continually growing, not shrinking. I’m never finished finding things to do in Chicago, whether that means digging into the city’s past or keeping up with its latest activities.

The book balances Chicago icons, like deep dish and Wrigley Field, with lesser-known local favorites. I was impressed with the breadth of neighborhoods represented, from Devon Avenue on the North Side down to 95th Street.

The tips are organized in five categories: Food and Drink, Music and Entertainment, Culture and History, Sports and Recreation, and Shopping and Fashion. Page also provides suggested itineraries like “Ferris Bueller’s Day Off” and “Satisfy Your Sweet Tooth.”

“These 100 things are a perfect way to begin to explore a never-full, always-evolving major metropolis.” – Molly Page

100 Things to Do in Chicago Before You Die is a great travel guide for Chicago visitors and residents alike. I consider myself a pretty seasoned Chicago explorer, and I was pleased to find 30 things I haven’t done yet! Thanks to Page, I’ll be taco tasting at El Milagro Tortilleria and taking an app-led tour of Grant Park’s public art this summer.

To develop the list, Page consulted with travel professionals, concierges, the city’s tourism organization, and Chicagoans of all ages. She aimed for twenty items in each of the book’s five categories. Populating the list was easy, she said, but narrowing the list down to 100 items was not.

When Page’s publisher suggested that Chicagoans should be considered as an audience for the book she was skeptical at first. But, “I made it a mission to find things that would surprise locals, and not make them roll their eyes,” she told us.

This strategy of surprising locals meant getting them out of their own neighborhoods. Page viewed the list options geographically to intentionally highlight a range of areas. “Chicago is a city of neighborhoods,” she said. “There’s such a different feel in each neighborhood. It wouldn’t be an accurate picture of the city if I only included the downtown Loop. That’s not what the city is about.”

Credit: Ryan Bourque

One place on the list that initially surprised Page was the Magic Parlour, a show led by a third-generation magician in the historic Palmer House Hilton, of all places. “I was most surprised that there are amazing things in this city that I never knew existed,” she told us.

A Chicago transplant of five years originally from St. Louis, Page credits her docent training at the Chicago Architecture Foundation for transforming her from a tourist to a student of the city. She channeled the fresh perspective of a transplant to appreciate and celebrate the city in her writing.

“I’m a Chicagoan by choice. I choose to stay because there’s always something new to eat, experience, and do.” – Molly Page

What’s Page’s top recommendation for Chicago visitors? Depending on the weather she’ll send them for drinks with a view at the Signature Room or Cindy’s. For photography, she heads to the pier at 31st Street Beach. While she gives tourists a pass to stick to downtown on their first Chicago visit, Page stresses that experiencing the city outside of what’s seen on postcards means getting out to the neighborhoods.

Credit: Diana Nguyen

Inspired by 100 Things to do in Chicago Before You Die, we compiled a few of our new initiatives to shake up the summer.